As a Métis youth, Whitford spent his early years in Fort Smith and later in Yellowknife. Uncertain of where he wanted to take his career, he worked as a truck driver, deck hand, mechanic and welder before pursuing post-secondary education. In the mid-1970s, Whitford was inspired to continue studies at the University of Calgary, obtaining a Bachelor degree in Social Work in 1977. It was during that time that Whitford's interest in politics was sparked, and he sought and won election to Fort Smith's town council. He continued to pursue municipal politics while working as a recruitment and training specialist, marriage councillor, Notary Public and Justice of the Peace in Fort Smith after graduating from the University of Calgary.
Whitford first entered provincial politics in 1988, when he was elected to the Northwest Territories' Legislative Assembly, serving as the Minister of Health and Social Services. He was elected Speaker of the House in January 2000. During his 12 years in the Assembly, Whitford represented the territorial government as a delegate in Britain, Europe, Australia, New Zealand and Africa. In addition to his political achievements, Whitford has been involved extensively in community work as a long-term Rotary Club member, past president of the Northwest Territories Canada Day Committee, and as a volunteer auctioneer and fundraiser in Fort Smith.
In 2004, Whitford began his tenure as Deputy Commissioner under Glenna Hansen. Although he had intended initially to retire from political life, he accepted the appointment as the Northwest Territories' next commissioner when Hansen's term ended, and he was installed as the 15th Commissioner on 29 April 2005.